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. Author manuscript; available in PMC: 2011 Apr 6.
Published in final edited form as: Pure Appl Chem. 2010 Apr 6;82(9):1735–1748. doi: 10.1351/pac-con-09-11-14

Scheme 9.

Scheme 9

Attempts to promote 1,2 alkyl shift of 68 to desired product 69. Key: (a) N-Acyl transfer: TFAA, toluene, 4Å MS, 100 °C, 4h, decomposition; (b) “retro-Woodward”: pyridine, Et3N, CH2Cl2, up to 50 °C, recovered SM; (c) Lewis acid, toluene, up to 80 °C, up to 18h, no reaction; (d) Cs2CO3, MeCN, 120 °C, 2h, decomposition; (e) CSA, CH2O, MeOH, 3Å MS, up to 160 °C, 2h, recovered SM.